Exclusive Hollywood Casino Vacation Deals

Hollywood Casino vacation package deals

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,124, price is now $671 per person
$671
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
This hotel features an outdoor pool and a 24-hour gym. Families will appreciate the waterslide, onsite laundry facilities, and in-room childcare. Guests will appreciate free perks like free self parking and WiFi in public areas.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,009, price is now $903 per person
$903
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
A marina, 3 restaurants, and 6 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a waterslide, and barbecue grills are available on site.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $2,088, price is now $1,004 per person
$1,004
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
This smoke-free resort features a private beach, a full-service spa, and a marina. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,457, price is now $914 per person
$914
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Families will appreciate the onsite laundry facilities and in-room childcare.
Esmeralda Resort

Esmeralda Resort

4 out of 5
Save 100% on your flight
Price was $1,266, price is now $845 per person
$845
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
This hotel features 15 outdoor pools, a restaurant, and a bar/lounge. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Families will appreciate the playground and onsite laundry facilities.
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,557, price is now $1,057 per person
$1,057
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
A full-service spa, an outdoor pool, and a restaurant are all featured at this resort. Enjoy the gym and perks like free valet parking and a free airport shuttle. There's a bar/lounge on site, and concierge services and free newspapers are also provided.

Frequently asked questions

How much are vacation packages to Hollywood Casino?
Let Travelocity take all the stress out of organizing your next big trip to Hollywood Casino. Book our awesome $671 package deal and save both money and time. With your hotel and flights sorted, you can concentrate on the fun parts of your adventure — like visiting those must-do attractions!
Where can I get the best vacation package deals for Hollywood Casino?
Travelocity has endless ways to score an awesome Hollywood Casino package deal. Select from as many as 400 partner airlines and 1,000,000 properties around the globe and craft a vacation package that's suited to you. With almost endless choice, it's time to start planning your next big adventure.
Why should I purchase my Hollywood Casino vacation package with Travelocity?
By booking your flights, hotel, activities and car rental altogether, you'll save time and money. We have a dedicated team of experts available 24/7, and you'll know that you're always getting the lowest price possible with our Price Match Guarantee. So, what's stopping you? Book the vacation of your dreams today and get packing!

Top Hollywood Casino hotel deals

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
$239 nightly
The price is $250 total per night
$250 total
May 14 - May 15
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and a marina. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site.
On private beach
Pool
Hilton Vacation Club Flamingo Beach St. Maarten

Hilton Vacation Club Flamingo Beach St. Maarten

4 out of 5
Pelican Key, Simpson Bay, 6 Billy Folly Simpson Bay
$147 nightly
The price is $155 total per night
$155 total
May 18 - May 19
Total with taxes and fees
This resort features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the gym and perks like free self parking and free WiFi. A 24-hour business center, a snack bar/deli, and laundry facilities are also on offer.
Pool
Parking included
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Billy Folly Road No. 37A Simpson Bay
$281 nightly
The price is $295 total per night
$295 total
May 12 - May 13
Total with taxes and fees
A marina, 3 restaurants, and 6 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and a waterslide, and barbecue grills are available on site.
Pool
Parking included
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.